Method for producing actinic ray-sensitive or radiation-sensitive resin composition, pattern forming method, method for producing electronic device, and method for producing onium salt

Abstract

A method for producing an actinic ray-sensitive or radiation-sensitive resin composition, the method including passing a solution including an acid compound having a pKa of 2.0 or more through a column packed with an ion-exchange resin, producing an onium salt by using the acid compound having been passed through the column, and mixing together the onium salt and a resin that undergoes an increase in polarity due to action of acid.

What is claimed is: 
     
         1 . A method for producing an actinic ray-sensitive or radiation-sensitive resin composition, the method comprising:
 passing a solution including an acid compound (CA) having a pKa of 2.0 or more, through a column packed with an ion-exchange resin;   producing an onium salt (C) by using the acid compound (CA) having been passed through the column; and   mixing together the onium salt (C) and a resin (A) that undergoes an increase in polarity due to action of acid.   
     
     
         2 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the ion-exchange resin has, as an ion-exchange group, a strongly acidic cation-exchange group. 
     
     
         3 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 2 , wherein the strongly acidic cation-exchange group is a sulfonic group. 
     
     
         4 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the acid compound (CA) has a pKa of 3.0 or more. 
     
     
         5 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the acid compound (CA) is a carboxylic acid or a phenol. 
     
     
         6 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the acid compound (CA) is a compound represented by General formula (CA1) or (CA2) below, 
       
         
           
           
               
               
           
         
         in General formula (CA1), 
         j represents 0 or 1, 
         Q C1  represents a substituent, 
         m1 and m2 each independently represent 0 or 1, 
         m3 represents an integer of 0 or more and (6+2j−m1−m2) or less, 
         a sum of m1 and m2 is 1 or 2, and 
         *'s each represent a direct bond connecting to the aromatic hydrocarbon described in General formula (CA1), and 
       
       
         
           
           
               
               
           
         
         in General formula (CA2), Q C2  represents an alkyl group or a cycloalkyl group. 
       
     
     
         7 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein a value provided by subtracting, from the pKa of the acid compound (CA), a pKa of an ion-exchange group of the ion-exchange resin is 3.0 or more. 
     
     
         8 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the ion-exchange resin has a degree of crosslinking of 10% or less. 
     
     
         9 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the actinic ray-sensitive or radiation-sensitive resin composition includes the onium salt (C) in an amount of 10 mass % or more relative to a total solid content. 
     
     
         10 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the actinic ray-sensitive or radiation-sensitive resin composition further contains a compound (B) that generates acid in response to irradiation with an actinic ray or radiation, and
 the actinic ray-sensitive or radiation-sensitive resin composition has a mass-based content A C  of the onium salt (C) and a mass-based content A B  of the compound (B), and satisfies A C :A B =1.4 to 4.1.   
     
     
         11 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the resin (A) has at least one selected from the group consisting of a repeating unit represented by General formula (A1) below, a repeating unit represented by General formula (A2) below, and a repeating unit represented by General formula (A3) below, 
       
         
           
           
               
               
           
         
         in General formula (A1), R a1 , R a2 , and R a3  each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, L a1  represents a single bond or a divalent linking group, Ar a1  represents an aromatic ring group, R a4  represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, R a5  and R a6  each independently represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, R a4  and R a5  may be linked together to form a ring, and Ar a1  may be linked with R a3  or R a4  to form a ring, 
         in General formula (A2), R a7 , R a8 , and R a9  each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, L a2  represents a single bond or a divalent linking group, Ar a2  represents an aromatic ring group, R a10 , R a11 , and R a12  each independently represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, and two of R a10 , R a11 , and R a12  may be linked together to form a ring, and 
         in General formula (A3), R a13 , R a14 , and R a15  each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, L a3  represents a single bond or a divalent linking group, Ar a3  represents an aromatic ring group, R a16 , R a17 , and R a18  each independently represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, and two of R a16 , R a17 , and R a18  may be linked together to form a ring. 
       
     
     
         12 . The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 , wherein the resin (A) has a repeating unit having a group that generates acid in response to irradiation with an actinic ray or radiation. 
     
     
         13 . A pattern forming method comprising
 forming a resist film on a substrate by an actinic ray-sensitive or radiation-sensitive resin composition produced by the method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to  claim 1 ,   exposing the resist film, and   developing the exposed resist film by a developer.   
     
     
         14 . A method for producing an electronic device, the method comprising the pattern forming method according to  claim 13 . 
     
     
         15 . A method for producing an onium salt, the method comprising:
 passing a solution including an acid compound (CA) having a pKa of 2.0 or more, through a column packed with an ion-exchange resin; and   producing an onium salt (C) by using the acid compound (CA) having been passed through the column.